GB952973A - A process for the production of unsaturated esters and alcohols - Google Patents
A process for the production of unsaturated esters and alcoholsInfo
- Publication number
- GB952973A GB952973A GB13167/62A GB1316762A GB952973A GB 952973 A GB952973 A GB 952973A GB 13167/62 A GB13167/62 A GB 13167/62A GB 1316762 A GB1316762 A GB 1316762A GB 952973 A GB952973 A GB 952973A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acetate
- isopentenyl
- higher boiling
- radical
- ester
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 150000002148 esters Chemical class 0.000 title abstract 6
- 238000000034 method Methods 0.000 title abstract 3
- 150000001298 alcohols Chemical class 0.000 title abstract 2
- 238000004519 manufacturing process Methods 0.000 title abstract 2
- -1 carboxylic acid ester radical Chemical group 0.000 abstract 15
- XXIKYCPRDXIMQM-UHFFFAOYSA-N Isopentenyl acetate Chemical compound CC(C)=CCOC(C)=O XXIKYCPRDXIMQM-UHFFFAOYSA-N 0.000 abstract 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 abstract 7
- GLZPCOQZEFWAFX-UHFFFAOYSA-N Geraniol Chemical compound CC(C)=CCCC(C)=CCO GLZPCOQZEFWAFX-UHFFFAOYSA-N 0.000 abstract 6
- 238000009835 boiling Methods 0.000 abstract 6
- CZVXBFUKBZRMKR-UHFFFAOYSA-N lavandulol Chemical compound CC(C)=CCC(CO)C(C)=C CZVXBFUKBZRMKR-UHFFFAOYSA-N 0.000 abstract 4
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 abstract 3
- 238000007127 saponification reaction Methods 0.000 abstract 3
- 235000007586 terpenes Nutrition 0.000 abstract 3
- CZVXBFUKBZRMKR-JTQLQIEISA-N (R)-lavandulol Natural products CC(C)=CC[C@@H](CO)C(C)=C CZVXBFUKBZRMKR-JTQLQIEISA-N 0.000 abstract 2
- MHNNAWXXUZQSNM-UHFFFAOYSA-N 2-methylbut-1-ene Chemical compound CCC(C)=C MHNNAWXXUZQSNM-UHFFFAOYSA-N 0.000 abstract 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 abstract 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 abstract 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 abstract 2
- GLZPCOQZEFWAFX-JXMROGBWSA-N Nerol Natural products CC(C)=CCC\C(C)=C\CO GLZPCOQZEFWAFX-JXMROGBWSA-N 0.000 abstract 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 239000000470 constituent Substances 0.000 abstract 2
- HYNGAVZPWWXQIU-UHFFFAOYSA-N lavandulyl acetate Chemical compound CC(C)=CCC(C(C)=C)COC(C)=O HYNGAVZPWWXQIU-UHFFFAOYSA-N 0.000 abstract 2
- XMGQYMWWDOXHJM-UHFFFAOYSA-N limonene Chemical compound CC(=C)C1CCC(C)=CC1 XMGQYMWWDOXHJM-UHFFFAOYSA-N 0.000 abstract 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 abstract 2
- SDOFMBGMRVAJNF-KVTDHHQDSA-N (2r,3r,4r,5r)-6-aminohexane-1,2,3,4,5-pentol Chemical compound NC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO SDOFMBGMRVAJNF-KVTDHHQDSA-N 0.000 abstract 1
- OKKBNXNEJFEISZ-UHFFFAOYSA-N (3-acetyloxy-3,7-dimethyloct-6-enyl) acetate Chemical compound C(C)(=O)OC(CCC=C(C)C)(CCOC(C)=O)C OKKBNXNEJFEISZ-UHFFFAOYSA-N 0.000 abstract 1
- MUZPKOFBDLINTJ-UHFFFAOYSA-N (5-methyl-2-prop-1-en-2-ylhex-5-enyl) propanoate Chemical compound CCC(=O)OCC(C(C)=C)CCC(C)=C MUZPKOFBDLINTJ-UHFFFAOYSA-N 0.000 abstract 1
- 239000001074 1-methoxy-4-[(E)-prop-1-enyl]benzene Substances 0.000 abstract 1
- BBTRQSDRTFFNSW-UHFFFAOYSA-N 3-methylbut-3-enyl benzoate Chemical compound CC(=C)CCOC(=O)C1=CC=CC=C1 BBTRQSDRTFFNSW-UHFFFAOYSA-N 0.000 abstract 1
- KCZPANQDJOYLQI-UHFFFAOYSA-N 4,8-dimethylnon-4-enoic acid Chemical compound CC(C)CCC=C(C)CCC(=O)O KCZPANQDJOYLQI-UHFFFAOYSA-N 0.000 abstract 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 abstract 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 abstract 1
- FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 abstract 1
- KUMOJCWXYXGQHW-UHFFFAOYSA-N C(C)(=O)OCC=C(/C)CCC=C(C)C.CC(C)=CCCC(=CCO)C Chemical compound C(C)(=O)OCC=C(/C)CCC=C(C)C.CC(C)=CCCC(=CCO)C KUMOJCWXYXGQHW-UHFFFAOYSA-N 0.000 abstract 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 abstract 1
- GLZPCOQZEFWAFX-YFHOEESVSA-N Geraniol Natural products CC(C)=CCC\C(C)=C/CO GLZPCOQZEFWAFX-YFHOEESVSA-N 0.000 abstract 1
- 239000005792 Geraniol Substances 0.000 abstract 1
- VHVOLFRBFDOUSH-NSCUHMNNSA-N Isosafrole Chemical compound C\C=C\C1=CC=C2OCOC2=C1 VHVOLFRBFDOUSH-NSCUHMNNSA-N 0.000 abstract 1
- VHVOLFRBFDOUSH-UHFFFAOYSA-N Isosafrole Natural products CC=CC1=CC=C2OCOC2=C1 VHVOLFRBFDOUSH-UHFFFAOYSA-N 0.000 abstract 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 abstract 1
- WNHXJHGRIHUOTG-ONEGZZNKSA-N [(e)-but-2-enyl] acetate Chemical compound C\C=C\COC(C)=O WNHXJHGRIHUOTG-ONEGZZNKSA-N 0.000 abstract 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 abstract 1
- 150000001242 acetic acid derivatives Chemical class 0.000 abstract 1
- 239000003377 acid catalyst Substances 0.000 abstract 1
- 125000001931 aliphatic group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- WUOACPNHFRMFPN-UHFFFAOYSA-N alpha-terpineol Chemical compound CC1=CCC(C(C)(C)O)CC1 WUOACPNHFRMFPN-UHFFFAOYSA-N 0.000 abstract 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 abstract 1
- 229910052796 boron Inorganic materials 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- WJSDHUCWMSHDCR-VMPITWQZSA-N cinnamyl acetate Natural products CC(=O)OC\C=C\C1=CC=CC=C1 WJSDHUCWMSHDCR-VMPITWQZSA-N 0.000 abstract 1
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 abstract 1
- 239000003085 diluting agent Substances 0.000 abstract 1
- XQRLCLUYWUNEEH-UHFFFAOYSA-N diphosphonic acid Chemical compound OP(=O)OP(O)=O XQRLCLUYWUNEEH-UHFFFAOYSA-N 0.000 abstract 1
- 150000002168 ethanoic acid esters Chemical class 0.000 abstract 1
- 229940113087 geraniol Drugs 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 239000012442 inert solvent Substances 0.000 abstract 1
- 235000001510 limonene Nutrition 0.000 abstract 1
- 229940087305 limonene Drugs 0.000 abstract 1
- 125000005394 methallyl group Chemical group 0.000 abstract 1
- RUVINXPYWBROJD-UHFFFAOYSA-N para-methoxyphenyl Natural products COC1=CC=C(C=CC)C=C1 RUVINXPYWBROJD-UHFFFAOYSA-N 0.000 abstract 1
- NIXKBAZVOQAHGC-UHFFFAOYSA-N phenylmethanesulfonic acid Chemical class OS(=O)(=O)CC1=CC=CC=C1 NIXKBAZVOQAHGC-UHFFFAOYSA-N 0.000 abstract 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 abstract 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 abstract 1
- 229930004725 sesquiterpene Natural products 0.000 abstract 1
- RUVINXPYWBROJD-ONEGZZNKSA-N trans-anethole Chemical compound COC1=CC=C(\C=C\C)C=C1 RUVINXPYWBROJD-ONEGZZNKSA-N 0.000 abstract 1
- 235000005074 zinc chloride Nutrition 0.000 abstract 1
- 239000011592 zinc chloride Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B9/00—Essential oils; Perfumes
- C11B9/0061—Essential oils; Perfumes compounds containing a six-membered aromatic ring not condensed with another ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/28—Preparation of carboxylic acid esters by modifying the hydroxylic moiety of the ester, such modification not being an introduction of an ester group
- C07C67/293—Preparation of carboxylic acid esters by modifying the hydroxylic moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B9/00—Essential oils; Perfumes
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B9/00—Essential oils; Perfumes
- C11B9/0007—Aliphatic compounds
- C11B9/0015—Aliphatic compounds containing oxygen as the only heteroatom
- C11B9/0019—Aliphatic compounds containing oxygen as the only heteroatom carbocylic acids; Salts or esters thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
A process for the production of unsaturated esters and alcohols comprises reacting an ester of formula: <FORM:0952973/C2/1> where X is a carboxylic acid ester radical, R1 a hydrogen atom or a p- or sec alkyl or alkenyl radical, and R2 a p- or secalkyl or alkenyl radical or phenyl radical, with an aliphatic or cycloaliphatic olefinically unsaturated compound which may be an olefine or an olefine substituted by an ester, ether or hydroxy group in the presence of a Friedel Crafts catalyst. R1 may be methyl-, ethyl-, propyl, propenyl- and 4-methyl-pent -3-enyl-radical and 4, 8-dimethyl-nona-3.7 dienyl, and the ester radical may be acetate, propionate, butyrate or benzoate and esters mentioned are a , a -di methylallyl (prenyl) acetate, crotyl acetate or cinnamyl acetate. The olefines and substituted olefines may be isobutene, styrene, a -methylstyrene, anethol, isosafrol, limonene, cyclohexane, propylene, isoprene and butadiene, or compounds of the formula of the first component such as, g g-dimethallyl, methallyl, 2-methyl-but-1-ene, isopentenyl and geranyl acetates. Orthophosphoric, pyrophosphoric, dichloracetic, perchloric, sulphuric, boron trifluofride, zinc chloride or toluene sulphonic acids are mentioned as suitable cataysts and the process may be in inert solvent such as acetic acid esters. Examples describe the reaction of isobutylene with g , g -dimethylallyl (prenyl) acetate to form 2, 6dimethyl-hept -2- enyl-acetate together with higher boiling constituents; anhydrous g , g dimethallyl acetate with itselt, alone or in ethyl acetate diluent, to form oxydihydrolavandulydiacetate, lavandulyl acetate, and higher boiling point constituents; g , g 2-dimethallyl propionate with itself to form lavandulyl propionate, oxydihydro-lavandulyl dipropionate and a higher boiling residue; 2-methyl-but-1-ene-4- acetate with g , g -dimethallyl acetate to form terpene acetate (lavandulyl, alto- and iso-geranyl and neryl acetates), 2, 6-dimethyl oct-2- ene-6, 8-diol-diacetate and sesquiterpene acetate with higher boiling fractions; isopentenyl acetate and prenyl acetate in ethyl acetate or acetic acid to yield terpene acetate, geraniol-hydrate-diacetate and higher boiling point fractions; isopentenyl acetate and g g -dimethylallyl acetate with a pyrophosphonic acid catalyst (followed by) the saponification of the ester to form terpene alcohol (lavandulol, a C10 alcohol, iso-and altogeraniol, nerol, and geraniol); isopentenyl benzoate in ethl acetate followed by saponification to lavandulol, alto- and isogreraniol, nerol, and geranol; 2, 6-dimethylocta-2, 6-dien -8- ol (geranyl) acetate with isopentenyl acetate followed by saponification to fornesol; isopentenyl acetate and prenyl acetate to form terpene acetate, geraniol-hyrate, di-acetate and higher boiling components.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEH42206A DE1146487B (en) | 1961-04-05 | 1961-04-05 | Process for the production of unsaturated compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB952973A true GB952973A (en) | 1964-03-18 |
Family
ID=7154781
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB13167/62A Expired GB952973A (en) | 1961-04-05 | 1962-04-05 | A process for the production of unsaturated esters and alcohols |
Country Status (3)
| Country | Link |
|---|---|
| US (1) | US3210408A (en) |
| AT (1) | AT242115B (en) |
| GB (1) | GB952973A (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4061667A (en) * | 1974-01-09 | 1977-12-06 | Monsanto Company | Cis-2-methyl-oct-5-en-2-yl acetate |
| US4910321A (en) * | 1985-06-20 | 1990-03-20 | University Of Akron | Living catalysts, complexes and polymers therefrom |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2402485A (en) * | 1943-06-14 | 1946-06-18 | Shell Dev | Catalytic polymerization of unsaturated esters |
| US2834747A (en) * | 1953-11-23 | 1958-05-13 | Phillips Petroleum Co | Co-polymers from aryl-substituted butenyl alcohols, ethers, and esters and a conjugated diene, compositions containing same, and method of making |
| US3021359A (en) * | 1959-03-20 | 1962-02-13 | Hoffmann La Roche | Unsaturated acyclic esters, and method of producing same |
-
1962
- 1962-03-30 US US183739A patent/US3210408A/en not_active Expired - Lifetime
- 1962-04-02 AT AT266262A patent/AT242115B/en active
- 1962-04-05 GB GB13167/62A patent/GB952973A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| US3210408A (en) | 1965-10-05 |
| AT242115B (en) | 1965-08-25 |
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